Winslow was a Duke blue devil for his first two years of college, however, he's relocated for the 2026 season now at the University of North Carolina. At Chapel Hill, Winslow is putting up by far the best year of his career. He owns a batting average north of .300, his bat-to-ball skills have jumped a grade, the exit velocities have ticked up as well.
Winslow has a thick, physical frame with some bat speed. He's at his best when he catches the ball out in front. Pulling the baseball in the air is something that he's always excelled at. There's some stiffness to the swing at times especially against spin, but Winslow rarely chases and draws plenty of walks. Behind the plate Winslow has held runners quite well this year.